Lithium hydroxide, monohydrate → HCID 69220851, compound

HRID 854010Notes

Reaction equation

HRID 854010 reaction equation
C([O:8][C:9]([CH:11]1[CH2:15][CH:14]([CH2:16][CH:17]=[CH:18][CH2:19][CH3:20])[CH2:13][N:12]1[CH2:21][C:22]1[N:23]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:24]=[CH:25][N:26]=1)=[O:10])C1C=CC=CC=1.C1COCC1.O.O.[OH-].[Li+]>O>[CH2:27]([N:23]1[CH:24]=[CH:25][N:26]=[C:22]1[CH2:21][N:12]1[CH2:13][CH:14]([CH2:16][CH:17]=[CH:18][CH2:19][CH3:20])[CH2:15][CH:11]1[C:9]([OH:10])=[O:8])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 21881883Oxolane--water (1/1)HCID 69223569HCID 69223569, compound

Product 1

HCID 69220851HCID 69220851, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 1-(1-benzyl-1H-imidazol-2-ylmethyl)-4-pent-2-enyl-pyrrolidine-2-carboxylic acid benzyl ester (257.2 mg, 0.6 mmol, 1 equiv) in a 4:1 THF/H2O (8 mL), at room temperature, was added lithium hydroxide monohydrate (250 mg, 5.96 mmol, 10 equiv). The resulting reaction mixture was stirred at room temperature overnight, and evaporated to dryness. The residue obtained was dissolved in water (10 mL), and the pH of the resulting solution was adjusted to between 3 and 4, and extracted with EtOAc (3×100 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and evaporated to dryness, affording the acid product 1-(1-Benzyl-1H-imidazol-2-ylmethyl)-4-pent-2-enyl-pyrrolidine-2-carboxylic acid (202 mg, 98%): Rf=0.4 (7:2:1 CH2Cl2/hexanes/MeOH), KMnO4 visualization stain; MS (ESPOS): 355 [M+H]+; MS (ESNEG): 352 [M−H]−.

Workup

  1. customThe resulting reaction mixture
  2. customevaporated to dryness
  3. customThe residue obtained
  4. extractionextracted with EtOAc (3×100 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-423b3c76c1f041c68bf8b1ab55d7e127
Source dataset
uspto-grants-2007_08
Patent number
US07256177B2

Reaction notes

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